Dyeing of cellulose-containing textile material and novel dyes for use therein

ABSTRACT

A process for dyeing cellulose-containing textile material, wherein a dye of the general formula I    &lt;IMAGE&gt;  I  where R is an aliphatic, cycloaliphatic, araliphatic or aromatic radical and n is 0 or 1, and where the rings A, B and C may be substituted and may carry a fused ring, is used. On cotton and especially on cotton/polyester union fabrics, the process according to the invention gives very fast, especially very lightfast, dyeings.

The present invention relates to a process for dyeingcellulose-containing textile material, and to certain novel dyes for usein this process. According to the invention there is provided a processfor dyeing cellulose-containing textile material, wherein a dye of thegeneral formula I ##STR2## where R is an aliphatic, cycloaliphatic,araliphatic or aromatic radical and n is 0 or 1, and where the rings A,B and C may be substituted and/or may carry a fused ring, is used. Agroup of technically valuable compounds corresponds to formula I wherethe radical ##STR3##

Examples of radicals R are alkenyl, C₁ -C₁₂ -alkyl, which may beinterrupted by oxygen and may be substituted by hydroxyl, chlorine,bromine, unsubstituted or substituted carbamyl, cyano, C₁ -C₈ -alkoxy,C₁ -C₄ -alkanoyl, benzoyl, C₁ -C₄ -alkanolyloxy, phenoxy orunsubstituted or substituted phenyl (eg. tolyl or chlorophenyl),cycloalkyl of 5 to 8 carbon atoms, or unsubstituted or methyl-, ethyl-or chlorine-substituted phenyl.

Specific examples of R are: CH₃, C₂ H₅, n--C₃ H₇, n--C₄ H₉, n--C₆ H₁₃,CH₂ --CH(C₂ H₅)C₄ H₉ --n, n--C₈ H₁₇, n--C₁₀ H₂₁, n--C₁₂ H₂₅, --C₂ H₄OCH₂ CH(C₂ H₅)C₄ H₉ --n, CH₂ CH═CH₂, --C₂ H₄ Cl, --C₂ H₄ Br, --C₂ H₄OCH₃, --C₂ H₄ OC₂ H₅, --C₂ H₄ OC₆ H₅, --C₆ H₁₁, --C₆ H₅, --C₆ H₄ CH₃,--C₆ H₄ Cl, --C₆ H₄ C₂ H₅, --CH₂ --C₆ H₅, --CH₂ --C₆ H₄ --CH₃, --CH₂ C₆H₄ Cl, --CH₂ C₆ H₃ Cl₂, CH₂ C₆ H₄ NO₂, --CH₂ --C₆ H₄ CN, --C₂ H₄ C₆ H₅,--C₃ H₆ C₆ H₅, C₂ H₄ OC₆ H₅, --C₃ H₆ --CN, --CH₂ --CONH₂, --CH₂CON(CH₃)₂, CH₂ CON(C₂ H₅)₂, CH₂ CONHC₆ H₅, --CH₂ CO₂ CH₃, --CH₂ CO₂ C₂H₅, --CH₂ CO₂ C₄ H₉, --CH₂ --CO--CH₃, CO₂ COC₆ H₅, --CH₂ --CH(OH)C₆ H₅,--CH₂ --CH(OH)CH₂ OC₆ H₅, CH₂ CH(OH)C₂ H₅, --C₂ H₄ OCOCH₃, --C₂ H₄ OCOC₃H₇, --CH₂ CH(C₂ H₅)OCOCH₃, CH₂ CH(C₂ H₅)OCOC₂ H₅, ##STR4## and --C₂ H₄OC₂ H₄ OC₆ H₅.

The ring B may, for example, be substituted by chlorine, bromine,methyl, ethyl, acetylamino, C₁ -C₄ -alkoxy or phenoxy or may carry afused benzo ring which is itself unsubstituted or substituted by methoxyor ethoxy.

Examples of substituents for the ring C include chlorine, methyl, ethyl,methoxy, ethoxy, phenyl and acetylamino.

Examples of substituents of the ring A are chlorine, bromine, methyl,trifluoromethyl, ethyl, hydroxyl, methoxy, ethoxy, phenoxy, nitro,cyano, phenylazo which is unsubstituted or substituted by methyl, ethyl,O(SO₂)_(n) R, chlorine, bromine, nitro or cyano, methylsulfonyl,ethyl-sulfonyl, phenylsulfonyl, SO₂ OR, COOR, ##STR5##

Examples of radicals R¹ are hydrogen. C₁ -C₄ -alkyl andhydroxyl-substituted or C₁ -C₄ -alkoxy-substituted C₂ -or C₃ -alkyl.

Certain of the dyes are novel compounds, in particular those which havethe formula I where R is a cycloaliphatic, araliphatic or aromaticradical. Araliphatic radicals R are preferred.

A compound of the formula I may be prepared by introducing the radical Ror RSO₂ into a compound of the formula II ##STR6## Conventional methodsmay be used. For example, suitable reactants for alkylating the phenolicOH group are unsubstituted and substituted alkylene oxides,unsubstituted and substituted alkyl chlorides and bromides,unsubstituted and substituted dialkyl sulfates and unsubstituted andsubstituted esters of aliphatic and aromatic sulfonic acids.

The etherificational manner, for example, in an aqueous-alkaline medium,in an alkaline, aqueous-organic medium or in an anhydrous organicsolvent, in the presence of an acid-binding agent. The reaction is mostadvantageously carried out at from 50° to 160° C., and in the case oflow-boiling alkylating agents or solvents an autoclave is used, wherenecessary.

Details of the method of preparation may be found in the Examples, whereparts and percentages are by weight, unless stated otherwise.

Suitable dyeing methods for applying the dyes of the formula I are, inparticular, those described in German Pat. No. 1,811,796 and GermanLaid-Open Applications Nos. DOS 2,524,243 and DOS 2,528,743, i.e. bycontacting the cellulose-containing textile material with water and anoxyethylene or oxypropylene compound to swell the cellulose fibers and,simultaneously or subsequently whilst the fibers are still swollen withthe dye.

EXAMPLE 1

17.6 parts of the dye C.I. Disperse Orange 13, 6.9 parts of potassiumcarbonate, 13 parts of 2-phenyl-ethyl bromide and 0.2 part of potassiumiodide in 120 parts of ethanol are refluxed for 5 hours. The product isfiltered off at room temperature and washed with ethanol and with water;16 parts of the dye of the formula ##STR7## are obtained.

10 parts of this dye are mixed with 100 parts of polyethylene oxide ofmolecular weight 300 and 790 parts of a 3% strength alginate thickenerbase to give an ink, with which a cotton fabric is printed by rotaryscreen printing. The fabric is then dried at 100° C., treated with hotair at 200° C. for 1 minute, rinsed cold, soaped at the boil, againrinsed cold and dried. A light-fast and washfast brownish orange printon a white ground is obtained.

EXAMPLE 2

52 parts of C.I. Disperse Orange 55, 103 parts of potassium carbonate,116.6 parts of β-phenoxyethyl chloride and 0.2 part of sodium iodide, ina mixture of 240 parts of methyl ethyl ketone and 300 parts ofN-methylpyrrolidone, are stirred for 5 hours at 100° C. The batch isthen stirred into water and the precipitate is filtered off, washed withwater and dried. 71 parts of the dye of the formula ##STR8## areobtained.

A 65:35 (weight/weight) polyester/cotton union fabric is treated with apaste which comprises 20 parts of the above dye, 120 parts of a reactionproduct of polyethylene oxide of molecular weight 300 with boric acid inthe molar ratio of 3:1 and 860 parts of a 10% strength alginatethickener base. The print is dried at 105° C. and then treated for 6minutes with live steam at 180° C. It is then rinsed with cold water,soaped at 80° C., rinsed cold and dried. A lightfast and washfastyellowish orange print on a white ground is obtained.

EXAMPLE 3

40 parts of a 45% strength aqueous paste of C.I. Disperse Orange 55 arestirred into 500 parts of N-methyl-pyrrolidone. 25 parts of benzenesulfochloride and simultaneously, 60 parts by volume of 10% strengthsodium hydroxide solution are added dropwise at 0°-20° C. After stirringfor 1 hour, a further 50 parts of benzene sulfochloride are added. Aftera few hours, the product is filtered off cold, washed with alcohol anddried. 33.5 parts of the dye of the formula ##STR9## are obtained.

A cotton fabric is roller-printed with a print paste which comprises 15parts of the above dye, 110 parts of polyethylene oxide of molecularweight 350, 30 parts of oleic acid diethanolamide and 845 parts of a 10%strength alginate thickener base. The print is dried at 100° C. and isthen fixed by treatment with hot air at 195° C. for 1 minute. Afterfinishing as described in Example 1, a very fast yellow print on a whiteground is obtained.

The following dyes are obtained similarly, and when applied to cottonand union fabric by the above methods give very fast dyeings.

    __________________________________________________________________________    Ex-                                                                           ample                                                                             Formula                                         Hue                       __________________________________________________________________________         ##STR10##                                      yellow                    5                                                                                  ##STR11##                                        "                       6                                                                                  ##STR12##                                        "                       7                                                                                  ##STR13##                                        "                       8                                                                                  ##STR14##                                      brownish yellow           9                                                                                  ##STR15##                                      yellow                    10                                                                                 ##STR16##                                        "                       11                                                                                 ##STR17##                                      brown                     12                                                                                 ##STR18##                                      reddish brown             13                                                                                 ##STR19##                                      reddish  brown            14                                                                                 ##STR20##                                      yellow                    15                                                                                 ##STR21##                                      yellow                    16                                                                                 ##STR22##                                      yellow                    17                                                                                 ##STR23##                                      yellow                    18                                                                                 ##STR24##                                      yellow                    __________________________________________________________________________

EXAMPLE 19

A mixture of 90 parts of the dye of the formula ##STR25## 600 parts ofN-methylpyrrolidone, 56 parts of potassium carbonate and 88.3 parts ofbenzyl chloride is stirred for 3 hours at 80° C. 750 parts of water areadded at room temperature and the precipitate is filtered off, washedwith water and dried; 100 parts of the dye of the formula ##STR26## areobtained.

A 65:35 (weight/weight) polyester/cellulose union fabric isscreen-printed with an ink which comprises 30 parts of the dye of theabove structure, 100 parts of a reaction product of polyethylene oxideof molecular weight 300 with boric acid, in a molar ratio 3:1, 30 partsof oleic acid diethanolamide and 840 parts of a 3% strength alginatethickener base, and the print is dried at 110° C. It is then treatedwith live steam at 185° C. for 5 minutes and is finished as described inExample 2. A fast orange print on a white ground is obtained.

The dyes mentioned in the Examples which follow can be converted to acommercial dye formulation as follows:

30 parts of dye, 6 parts of dispersant, 10 parts of humectant, 1 part ofdisinfectant and about 53 parts of water are milled in a stirred ballmill until the particle size is about 0.5 μm. The dye dispersion thusobtained has a food shelf life.

The substituents T¹ to T⁸ of the dyes listed in the Table which followsand the indices which precede the substituents in the columns of theTable, correspond to the formula (III).

      ##STR27##      III Example T.sup.1 T.sup.2 T.sup.3T.sup.4 T.sup.5 T.sup.6 T.sup.7     T.sup.8 Hue       20 H H H H H 3-CH.sub.3 H OC.sub.12 H.sub.25(n) yellow 21 " " " "  " "     " OC.sub.2 H.sub.4 C.sub.6      H.sub.5 " 22 " " " " " " " OCH(CH.sub.3)CH.sub.2 C.sub.6 H.sub.5 " 23 "     " " " " " " OCH.sub.2 CONH.sub.2 " 24 " " " " " " " OCH.sub.2 COC.sub.6     H.sub.5 " 25 2-CH.sub.3 OCH.sub.2 C.sub.6 H.sub.5 " " " 2-CH.sub.3 "     OCH.sub.2 C.sub.6 H.sub.5 golden yellow 26 " OCH.sub.2 CN " " " " "     OCH.sub.2 CN golden yellow 27 " OC.sub.2 H.sub.4 C.sub.6 H.sub.5 " " " "     " OC.sub.2 H.sub.4 C.sub.6 H.sub.5 golden yellow 28 " " " " " " "     OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 golden yellow 29 " OC.sub.8 H.sub.17     -n " " " " " OC.sub.8 H.sub.17N golden yellow 30 H H " " " " " OC.sub.12     H.sub.25 -n golden yellow 31 " " " " " " " OC.sub.2 H.sub.4 C.sub.6     H.sub.5 golden yellow 32 " " " " " " " OCH.sub.2 CONHC.sub.6 H.sub.5     golden yellow 33 " " " " " 3-CONH.sub.2 " OC.sub.2 H.sub.4 C.sub.6     H.sub.5 yellow 34 " " " " " 3-Cl " OCH.sub.2 C.sub.6 H.sub.5 golden     yellow 35 " " " " " 2-Cl " " golden yellow 36 " " " 2-CH.sub.3 5-OCH.sub.     3 " 5-Cl " yellowish          brown 37 " " " " " " " OCH.sub.2 COC.sub.6     H.sub.5yellowish          brown 38 " " " " " " " OCH.sub.2 CONH.sub.2     brownish          yellow 39 " " " " " " " OCH.sub.2 C.sub.6      H.sub.4(p-)NO.sub.2 brownish          yellow 40 " " " 2-Cl H " "     OC.sub.2 H.sub.4 C.sub.6 H.sub.5 golden          yellow 41 " " " " " " "     OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 golden          yellow 42 " " " " "     2-CH.sub.3 " OCH.sub.2 COC.sub.6 H.sub.5 brownish          yellow 43 " "     " 2-Br 6-Br H H OC.sub.2 H.sub.4 C.sub.6 H.sub.5 brownish     yellow 44 " OC.sub.6 H.sub.5 " 2-OCH.sub.3 5-OCH.sub.3 " " OCH.sub.2     O.sub.6 H.sub.5 reddish orange 45 " " " " " " " OCOC.sub.6 H.sub.5     orange 46 " " " " " " " OCONH.sub.2 " 47 " " " " " " " OC.sub.2 H.sub.4     C.sub.6 H.sub.5 reddish orange 48 " " " " " " " OCH.sub.2 C.sub.6        N     H.sub.4O.sub.2 -p reddish orange 49 "" " " " " " OCH.sub.2 CH(C.sub.2     H.sub.5)C.sub.4 H.sub.9 -p reddish orange 50 " " " 2-CH.sub.3 5-CH.sub.3     " " OCH.sub.2 C.sub.6 H.sub.5 brownish yellow 51 " " " " " " " OCH.sub.2     COC.sub.6 H.sub.5 brownish yellow 52 " " " " " " " OC.sub.2 H.sub.4     C.sub.6 H.sub.5 brownish          yellow 53 2-OH H 5-CH.sub.3 H H     2-CH.sub.3 " OCH.sub.2 C.sub.6 H.sub.5 brownish          yellow 54 " " "     " " " " OC.sub.2 H.sub.4 C.sub.6 H.sub.5 brownish          yellow 55 " "     " " " " " OCH.sub.2CH(CH.sub.3)C.sub.6 H.sub.5 brownish          yellow     56 2-CH.sub.3 OCH.sub.2 CH(CH.sub.3)C.sub.6 H.sub.5 H " " "" " golden           yellow 57 H      ##STR28##      H " " " " OC.sub.2 H.sub.4 C.sub.6      H.sub.5 orange 58 "     ##STR29##      " " " " " OCH.sub.2 CH(C.sub.2 H.sub.4)C.sub.4 H.sub.9 -n " 59 "      ##STR30##      " " " " " OC.sub.2 H.sub.4 OC.sub.6      H.sub.5 " 60 "     ##STR31##      " " " " " OC.sub.4 H.sub.9 -n " 61 " H " " " 2-OCH.sub.3 " OCH.sub.2     C.sub.6 H.sub.5 yellowish          orange 62 " " " " " 2-OC.sub.2     H.sub.5 " OC.sub.2 H.sub.4 C.sub.6 H.sub.5 yellowish          orange 63     " " " " " 3-NHCOCH.sub.3 " " golden          yellow 64 " " " " " " "     OCH.sub.2 C.sub.6 H.sub.5 golden          yellow 65 " NNC.sub.6 H.sub.5     " 2-CH.sub.3 5-CH.sub.3 3-CH.sub.3 " " brownish          orange66 " " "     " " 2-CH.sub.3 " OC.sub.2 H.sub.4 C.sub.6 H.sub.5 brownish     orange 67 " " " " 5-OCH.sub.3 " " " orange          brown 68 " " "     2-OCH.sub.3 " " " " brownish          red69 " " " " " " "OCH.sub.2     CH(C.sub.2 H.sub.5)C.sub.4 H.sub.9 -n brownish          red70 2-CH.sub.3     H " 2-CH.sub.3 H 3-CH.sub.3 " OCH.sub.2 C.sub.6 H.sub.4Cl-(o) golden          yellow 71 " " " " " " " OCH.sub.2 C.sub.6 H.sub.4 Cl-(p) golden          yellow72 " " " " "2-CH.sub.3 " "golden          yellow73 " " " " "     " " OCH.sub.2 C.sub.6 H.sub.4 Cl-(o) golden          yellow74 " " " " "     " " OCH.sub.2 COC.sub.6 H.sub.5 golden          yellow 75 H " " H "     2-NHCOCH.sub.3 " OCH.sub.2 C.sub.6 H.sub.5 golden          yellow 76 "     "" " " 2-Cl 5-Cl " golden          yellow 77 " " " " " " " OCH.sub.2     COC.sub.6 H.sub.5 golden         yellow78 " " " 2-OCH.sub.3 5-OCH.sub.3     H H " golden          yellow79 " OC.sub.2 H.sub.4 C.sub.6 H.sub.5 " " "     2-CH.sub.3 " OCH.sub.2 C.sub.6 H.sub.5 brownish         orange80 " " " "     " " " OC.sub.2 H.sub.4 C.sub.6 H.sub.5 brownish         orange 81 " " "     " " " " OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 brownish          orange82 " "     " " " " " OCH.sub.2 CH(C.sub.2 H.sub.5)C.sub.4 H.sub.9 -(n) brownish          orange83 " OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 " " " " " OCH.sub.2     CH(CH.sub.3)C.sub.6 H.sub.5 brownish          orange84 " " " " " " "     OC.sub.6 H.sub.13 -(n) brownish          orange85 " " " 2-CH.sub.3 " " "     OC.sub.2 H.sub.4 C.sub.6 H.sub.5 yellowish         brown 86 " " " "     5-CH.sub.3 " " " brownish          yellow87 " OC.sub.2 H.sub.4 C.sub.6     H.sub.5 " " " " " " brownish          yellow88 " H " " 5-OCH.sub.3 H "     OCH.sub.2 COC.sub.6 H.sub.5 golden          yellow89 " " " " " "     "OCH.sub.2 CH(CH.sub.3)C.sub.6 H.sub.5 golden          yellow90 "     NO.sub.2 " 2-OCH.sub.3 H " " OC.sub.2 H.sub.4 C.sub.6 H.sub.5 orange91 "     " " " " " "OCH.sub.2 COC.sub.6 H.sub.5 orange 92 " OCH.sub.2 C.sub.6     H.sub.5 " " " " " OCH.sub.2 C.sub.6 H.sub.5 brownish          yellow 93     " OCH.sub.2 COC.sub.6 H.sub.5 " " " " " OCH.sub.2 COC.sub.6 H.sub.5     brownish         yellow 94 " OC.sub.2 H.sub.4 C.sub.6 H.sub.5 " " " " "     OC.sub.2 H.sub.4 C.sub.6 H.sub.5 brownish          yellow95 2-CH.sub.3 "     " " "2-CH.sub.3 " " yellowish          brown 96 " OC.sub.6 H.sub.13 -n "     " " " " OC.sub.6 H.sub.13 -n yellowish          brown 97 " OCH.sub.2     CH(CH.sub.3)C.sub.6 H.sub.5 " " " " " OCH.sub.2 CH(CH.sub.3)C.sub.6     H.sub.5 yellowish          brown98 " OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 "     " " " " OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 yellowish         brown 99 "     OC.sub.2 H.sub.4 O.sub.6 H.sub.5 " 2-CH.sub.3 5-OCH.sub.3 " " OC.sub.2     H.sub.4 C.sub.6 H.sub.5 yellowish          brown100 " OCH.sub.2      CH(CH.sub.3)C.sub.6 H.sub.5 " " " " " OCH.sub.2 CH(CH.sub.3)C.sub.6     H.sub.5 yellowish          brown101 2-SO.sub.2 C.sub.6 H.sub.5 H "     "5-CH.sub.3 H " OCH.sub.2 C.sub.6 H.sub.5 brownish          yellow102 "     " " " " " " OC.sub.2 H.sub.4 C.sub.6 H.sub.5 brownish         yellow103     " " " " " 2-CH.sub.3 " " brownish          yellow104 " " " " " " "     OCH.sub.2 CH(C.sub.2 H.sub.5)C.sub.4 H.sub.9 -n brownish         yellow     105 2-OCH.sub.3 " SO.sub.2 N(C.sub.2      H.sub.5).sub.2 2-OCH.sub.3 5-OCH.sub.3 H " OCH.sub.2 C.sub.6 H.sub.5     reddish         orange106 " " " " " " " OC.sub.2 H.sub.4 C.sub.6 H.sub.5     reddish         orange107 " " " " " 2-CH.sub.3 "" reddish     orange108 " " " 2-CH.sub.3 5-CH.sub.3 " " " yellowish          orange109     " " " " " " " OCH.sub.2 CH(CH.sub.3).sub.2 yellowish         orange110     "" " " " " " OCH.sub.2 C.sub.6 H.sub.5 yellowish          orange111 " "     " " " H " OC.sub.2 H.sub.4 C.sub.6 H.sub.5 yellowish          orange112     """ 2-OCH.sub.3 "2-CH.sub.3 " " orange 113 H " H 2-Br 6-Br 2-Cl 5-Cl "     yellow114 " " " " " 2-CH.sub. 3 6-CH.sub.3 OC.sub.2 H.sub.4 C.sub.6     H.sub.5 brownish         yellow 115 2-Cl NO.sub.2 6-Cl 2-OCH.sub.3     5-OCH.sub.3 " H  " brown 116 " " " " " " " OCO.sub.2 C.sub.6 H.sub.5 "     117 " " " " " " " OCH.sub.2 CH(CH.sub.3)C.sub.6      H.sub.5 " 118 H O-C.sub.6 H.sub.5 H 2-CH.sub.3 " 2-Cl 5-Cl OC.sub.2     H.sub.4 C.sub.6 H.sub.5 yellowish         brown 119 " " " " " 2-CH.sub.3     H " orange 120 " OCH.sub.3 " 2-OCH.sub.3 " 3-C.sub.6 H.sub.5 " " " 121 "     " " " " " " OCH.sub.2 C.sub.6 H.sub.5 " 122 " CONHC.sub.3 H.sub.6     OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 " " " 2-CH.sub.3 5-H " reddish      orange 123 " " " " " " " OC.sub.2 H.sub.4 C.sub.6 H.sub.5 reddish        orange  124 " " " " " " " OC.sub.2 H.sub.5 reddish          orange     125 " " " " " " " OCH.sub.2CHOH.sub.2 reddish          orange 126 " " "     2-CH.sub.3 5-CH.sub.3 H " OCH.sub.2 C.sub.6 H.sub.5 golden     yellow 127 " " " " 5-OCH.sub.3 2-CH.sub.3" " orange 128 " " " " " " "     OC.sub.2 H.sub.4 C.sub.6 H.sub.5 orange 129 2-OCH.sub.3 OCH.sub.3 5-Cl "     5-CH.sub.3 " " OCH.sub. 2 C.sub.6 H.sub.4NO.sub.2 -(p) golden     yellow 130 2-OC.sub.6 H.sub.5 H " 2-OCH.sub.3 5-OCH.sub.3 2-CH.sub.3 H     OC.sub.2 H.sub.4 C.sub.6 H.sub.5 orange 131 " " " " " " " OC.sub.2     H.sub.4 OC.sub.6 H.sub.5 orange 132 H " H H H 3-C.sub.6 H.sub.5 " "     yellow 133 " " " " " " " OCH.sub.2 C.sub.6 H.sub.5 " 134 " OCH.sub.3 "     2-OCH.sub.3 5-NHCOCH.sub.3 2-CH.sub.3 " OC.sub.2 H.sub.4 C.sub.6 H.sub.5     orange 135 " " " " " " " OCH.sub.2 CH.sub.2 OC.sub.6 H.sub.5 " 136 "     SO.sub.2 N(C.sub.2 H.sub.5).sub.2 " 2-CH.sub.3 5-CH.sub.3 " " OC.sub.2     H.sub.4 C.sub.6 H.sub.5 golden          yellow 137 "  NO.sub.2 " H H     2-C.sub.6 H.sub.5 " " golden         yellow 138 H CONHC.sub.3 H.sub.6     OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 " 2-CH.sub.3 5-CH.sub.3 2-CH.sub.3 " "     golden          yellow 139 " " " " " " " OCH.sub.3 golden     yellow 140 2-OCH.sub.3 H " 2-NHCOCH.sub.3 H " " " brownish     yellow 141 H OC.sub.2 H.sub.5 " " " " " " brownish          yellow 142 " N    N     .sub.6 H.sub.5 " 2-CH.sub.3 5-CH.sub.3 2-CH.sub.3 " OCH.sub.2      CH(OH)CH.sub.2 OC.sub.6 H.sub.5 brownish          orange 143 " " " " "     "  " OC.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub.3 brownish     orange 144 " " " " " " " OC.sub.2 H.sub.4 -Br brownish          orange     145 " " " " " " " OCH.sub.2 COCH.sub.3 brownish          orange 146 " 41      " " " " " O(CH.sub.2).sub.3 Cl brownish          orange 147 " OC.sub.2     H.sub.5 " " " " " OCH.sub.2 CH(C.sub.2 H.sub.5)OCOC.sub.3 H.sub.7 golden             yellow 148 " " " " " " " OC.sub.2 H.sub.4 OCOCH.sub.3 golden          yellow 149 2-OCH.sub.3 O-C.sub.4 H.sub.9 -n " H H " " OC.sub.4     H.sub.9 -n golden          yellow 150 " OC.sub.2 H.sub.4      CH(CH.sub.3).sub.2 " " " " " OC.sub.2 H.sub.4 CH(CH.sub.3).sub.2 golden              yellow 151 " OC.sub.2 H.sub.4 OCH.sub.3 " " " " " OC.sub.2     H.sub.4 OCH.sub.3 golden          yellow 152 " OC.sub.2 H.sub.4 OC.sub.2     H.sub.5 " " " " " OC.sub.2 H.sub.4 OC.sub.2 H.sub.5 golden     yellow 153 " OC.sub.2 H.sub.4 OC.sub.3 H.sub.6 (n) " " " " " OC.sub.2     H.sub.4 OC.sub.3 H.sub.6 (n) goldenyellow154 " OC.sub.2 H.sub.4 OC.sub.4     H.sub.9 (n) " " " " " OC.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n) golden        yellow 155 H NNC.sub. 6 H.sub.5 H 2-CH.sub.3 5-CH.sub.3 3-OC.sub.2     H.sub.5 H OC.sub.9 H.sub.19 -(n) prange 156 " " " " " 2-CH.sub.3 5-Cl     OC.sub.6 H.sub.13 -(n) " 157 " " " " " 2-C.sub.2 H.sub.5 6-C.sub.2     H.sub.5 OC.sub.6 H.sub.13 -(n) brownish          orange 158 " OC.sub.6     H.sub.5 " " " 2-CH.sub.3 H OCH.sub.2 CH(OH)C.sub.6 H.sub.5 golden       yellow 159 " " " " " " " OCH.sub.2 CO.sub.2 C.sub.4 H.sub.9 golden          yellow 160 " " " " " " " OCH.sub.2 COCH.sub.3 golden     yellow 161 " NO.sub.2 " 2-OC.sub.6 H.sub.5 H " " OC.sub.2 H.sub.4     C.sub.6 H.sub.5 orange 162 " " " 2-OC.sub.4 H.sub.9 5-OC.sub.4 H.sub.9 "     " " red 163 " OC.sub.6 H.sub.5 " 2-OC.sub.2 H.sub.5 5-OC.sub.2 H.sub.5     2-CH.sub.3 H OC.sub.2 H.sub.4 C.sub.6 H.sub.5 brownish          orange     164 " CN " 2-OCH.sub.3 5-CH.sub.3 " " " orange 165 2-CF.sub.3 H "     2-CH.sub.3 " " " " brownish          yellow 166 2-Br " " " " " " "     yellow 167 2-Cl SO.sub.2 CH.sub.3 " 2-OCH.sub.3 " " " " orange 168 H     SO.sub.2 C.sub.6 H.sub.5 " " " " " " " 169 2-CO.sub.2 C.sub.10 H.sub.21     (n) H " 2-CH.sub.3 " " " OCH.sub.2 C.sub.6 H.sub.5 yellow 170 H OC.sub.6     H.sub.5 " 2-CH.sub.3 5-OCH.sub.3 2-Cl 5-Cl OC.sub.2 H.sub.4 OC.sub.6     H.sub.5 yellowish          brown 171 " OCH.sub.3 " 2-OCH.sub.3 5-NHCOCH.s     ub.3 " " " yellowish          brown 172 " " " " " " " OC.sub.2 H.sub.4     C.sub.6 H.sub.5 yellowish          brown 173 " OC.sub.2 H.sub.5 " " " "     " OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 yellowish          brown 174 "     OCH.sub.3 " " " 2-CH.sub.3 H OC.sub.2 H.sub.4 OC.sub.2 H.sub.4 OC.sub.6     H.sub.5 orange 175 " OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 " " " " "     OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 " 176 " H " H H " " OC.sub.2 H.sub.4     OC.sub.2 H.sub.4 OC.sub. 6      H.sub.5 golden          yellow 177 "     ##STR32##      " " " " " " orange 178 2-OCH.sub.3      ##STR33##      " 2-OCH.sub.3 5-CH.sub.3 " " OC.sub.2 H.sub.4 OC.sub.6      H.sub.5 brownishorange 179 "      ##STR34##      " " " " " OC.sub.2 H.sub.4 C.sub.6 H.sub.5 brownishorange 180 H " " " "     " " " brownish          orange 181 " " " 2-CH.sub.3 " " " " orange 182 "      ##STR35##      " " " " " OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 " 183 " " " 2-OCH.sub.3     5-OCH.sub.4 " " " reddish          orange 184 2-OCH.sub.3 " " " " " " "     reddish          orange 185 " " " " 5-NHCOCH.sub.3 " " " reddish      orange 186 H " " 2-NHCOCH.sub.3 H " " " orange 187 " " " " 5-OCH.sub.3     " " " " 188 2-OCH.sub.3 " " " H " " " brownish          yellow 189 " " "     " " " " OC.sub.2 H.sub.4 C.sub.6 H.sub.5 brownish          yellow 190     2-OC.sub.2      H.sub.5 " " " " " " " brownish          yellow 191 H OCH.sub.3 " " " "     " " brownish          yellow 192 " " " " " " " OC.sub.2 H.sub.4 OC.sub.6     H.sub.5 brownish          yellow 193 " " " " " " " O(C.sub.2 H.sub.4     O).sub.2 C.sub.6 H.sub.5 brownish          yellow 194 " OC.sub.2 H.sub.5     " " " " " OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 brownish          yellow 195     " OCH.sub.3 " " "  2-Cl 5-Cl " brownish          yellow 196 2-OCH.sub.3      ##STR36##      " 2-OCH.sub.3 5-CH.sub.3 " " " orangebrown 197 H OC.sub.2 H.sub.4     OC.sub.6 H.sub.5 " 2-NHCOCH.sub.3 H 2-CH.sub.3 H " brownish     yellow 198 2-OC.sub.6 H.sub.5 H 5-Cl 2-OCH.sub.3 5-OCH.sub.3 2-Cl 5-Cl "     brownish          yellow 199 " " " " " " " OC.sub.2 H.sub.4 C.sub.6     H.sub.5 brownish          yellow 200 " " " " 5-CH.sub.3 2-CH.sub.3 H "     yellowish          brown 201 " " H " " " " OC.sub.2 H.sub.4 OC.sub.6     H.sub.5 yellowish          brown 202 " " 5-Cl " " 2-Cl 5-Cl " brownish            yellow 203 " " " " 5-OCH.sub.3 2-CH.sub.3 5-CH.sub.3 " yellowish             brown 204 2-OC.sub.2 H.sub.5 " H " " " H O(C.sub.2      H.sub.4).sub.2 C.sub.6 H.sub.5 orange 205 2-CH.sub.3 OC.sub.2 H.sub.4     C.sub.6 H.sub.5 H 2-OCH.sub.3 " " " OC.sub.2 H.sub.4 C.sub.6 H.sub.5 "     206 " OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 " " " " " OC.sub.2 H.sub.4     OC.sub.6 H.sub.5 " 207 " " " 2-Br 6-Br " " " yellowish          brown     208 " OC.sub.2 H.sub.4 C.sub.6 H.sub.5 " " " " " OC.sub.2 H.sub. 4     C.sub.6 H.sub.5 yellowish          brown 209 " " " 2-Cl 5-Cl " " "     brownish          yellow 210 " O(C.sub.2 H.sub.4 O).sub.2 C.sub.6     H.sub.5 " " " " " O(C.sub.2 H.sub.4 O).sub.2 C.sub.6 H.sub.5 brownish           yellow 211 2-OCH.sub.3      ##STR37##      5-OCH.sub.3 " 5-CH.sub.3 2-CH.sub.3 " " orange 212 " " 5-CH.sub.3     2-OCH.sub.3 5-OCH.sub.3 " " " " 213 "      ##STR38##      5-OCH.sub.3 " " " " OC.sub.2 H.sub.4 C.sub.6 H.sub.5 reddish orange 214     2-CH.sub.3 OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 H 2-Br 6-Br " " OC.sub.2     H.sub.4 OC.sub.6 H.sub.5 brownish          yellow 215 " OC.sub.2 H.sub.4     C.sub.6 H.sub.5 " " " " " OC.sub.2 H.sub.4 C.sub.6 H.sub.5 brownish         yellow 216 " " " 2-Cl 5-Cl " " " brownish          yellow 217 "     OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 " " " " " OC.sub.2 H.sub.4 OC.sub.6     H.sub.5 brownish          yellow 218 " O(C.sub.2 H.sub.4 O).sub.2     C.sub.6 H.sub.5 " " 6-Cl " " O(C.sub.2 H.sub.4 O).sub.2 C.sub.6 H.sub.5     brownish          yellow 219 2-OCH.sub.3      ##STR39##      5-OCH.sub.3 " 5-Cl " " OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 brownishorange     220 3-CO.sub.2 CH.sub.3 CO.sub.2 CH.sub.3 H 2-OCH.sub.3 5-CH.sub.3     2-Cl5-Cl " brownish          yellow 221 " " " " 5-OCH.sub.3 " " "     yellowish          brown 222 3-OC.sub.2 H.sub.4 C.sub.6 H.sub.5 H " " "     2-CH.sub.3 H OC.sub.2 H.sub.4 C.sub.6 H.sub.5 orange 223 3-OC.sub.2     H.sub.4 OC.sub.6 H.sub.5 " " " " " "OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 "     224 " " " 2-CH.sub.3 " " " " " 225 " " " " 5-CH.sub.3 " " " golden        yellow 226 " " " 2-OCH.sub.3 5-NHCOCH.sub.3 " " " orange 227 3-OC.sub.     2 H.sub.5 " " " " " " OC.sub.2 H.sub.5 " 228 3-OC.sub.2 H.sub.4 OC.sub.6     H.sub.5 " " " 5-OCH.sub.3 2-Cl 5-Cl OC.sub.2 H.sub.4 OC.sub.6 H.sub.5     yellowish          brown 229 " " " 2-CH.sub.3 " " " " brownish     yellow 230 " OC.sub.6 H.sub.5 " " " " " OC.sub.2 H.sub.4 C.sub.6 H.sub.5     yellowish brown 231 " OC.sub.6 H.sub.4 -p-Cl " " " " " " yellowish brown     232 " " " " " " " OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 yellowigh brown 233     " OC.sub.6 H.sub.5 " " 5-CH.sub.3 H H " golden yellow 234 " OC.sub.6     H.sub.4 -p-Cl " " " " " " golden yellow 235 " " " " " " " OC.sub.2     H.sub.4 C.sub.6 H.sub.5 golden yellow 236 " " " " " 2-Cl 5-Cl  OC.sub.2     H.sub.4 OC.sub.6 H.sub.5 golden yellow 237 " " " " " " " OC.sub.2     H.sub.4 C.sub.6 H.sub.5 golden yellow 238 " " " " " 2-CH.sub.3 H "golden     yellow 239 " " " " " 2-C.sub.6 H.sub.5 " " golden yellow 240 " " " " " "     " OC.sub.2 H.sub.4 OC.sub.6      H.sub.5 golden yellow 241 " " " " " 2-CH.sub.3 " " golden yellow 242 "     OC.sub.6 H.sub.5 " " " 2-Cl 5-Cl " golden yellow 243 " " " " " " "     OC.sub.2 H.sub.4 C.sub.6 H.sub.5 golden yellow 244 " " " " " 2-C.sub.6     H.sub.5 H " golden yellow 245 " " " " " " " OC.sub.2 H.sub.4 OC.sub.6     H.sub.5 golden yellow 246 " " " " " 3-CH.sub.3 " " golden yellow 247 " "     " " " " " OC.sub.2 H.sub.4 C.sub.6 H.sub.5 golden yellow 248 " " " " " H     " OSO.sub.2 C.sub.6 H.sub.5 golden yellow 249 " " " " 5-OCH.sub.3 " " "     golden          yellow 250 " " " " " 2-CH.sub.3 " OSO.sub.2 C.sub.6     H.sub.4CH.sub.3 (p) golden          yellow 251 " OC.sub.6 H.sub.4Cl(p) "     " " " " " golden          yellow 252 " " " 2-OCH.sub.3 " " " " orange     253 " OC.sub.6 H.sub.5 "  " " H " OSO.sub.2 C.sub.6 H.sub.5 " 254 " " "     " " " " OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 bright red 255 " " " " " " "     OC.sub.2 H.sub.4 OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 bright red 256 " " "     " " 2-CH.sub.3 " OC.sub.2 H.sub.4 C.sub.6 H.sub.5 " 257 " " " " " " "     OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 " 258 " " " " " 3-CH.sub.3 " " " 259 "     " " " " 2-C.sub.6 H.sub.5 " " orange 260 " " " " " 2-Cl 5-Cl " " 261 "     OC.sub.6 H.sub.4Cl(p) " " " H H " bright red 262 " "  " " " " " OC.sub.2     H.sub.2 C.sub.6 H.sub.5 " 263 " " " " " 2-C.sub.6 H.sub.5 " OC.sub.2     H.sub.4 C.sub.6 H.sub.5 orange 264 " " " " " " " OC.sub.2 H.sub.4     OC.sub.6 H.sub.5 " 265 " " " " " 2-CH.sub.3 " " bright red 266 " " " " "     " " OC.sub.2 H.sub.4 C.sub.6 H.sub.5 " 267 " " " " " 3-CH.sub.3 " " "     268 " " " " " " " OC.sub.2 H.sub.4 OC.sub.6      H.sub.5 " 269 " " " 2-OC.sub.2 H.sub.5 5-OC.sub.2 H.sub.5 H H " " 270 "     " " " " " " OC.sub.2 H.sub.4 C.sub.6 H.sub.5 bright red 271 " " " " " "     " OSO.sub.2 C.sub.6 H.sub.5 orange 272 " " " " " 2-CH.sub.3 " " " 273 "     " " " " " " OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 bright red 274 " OC.sub.6     H.sub.5 " " " " " " " 275 " " " " " H H " " 276 " " " " " " " OC.sub.2     H.sub.4 C.sub.6 H.sub.5 " 277 " " " " " 2-Cl 5-Cl " orange 278 " " " " "     2-C.sub.6 H.sub.5 H " " 279 " " " " " 3-CH.sub.3 " " bright red 280 " "     " " "  " " OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 " 281 " " " " " H "     OC.sub.2 H.sub.4 OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 " 282 " " " " " " "     OSO.sub.2 C.sub.6 H.sub.4CH.sub.3      (p) orange 283 " " " " " " " OSO.sub.2C.sub.6 H.sub.4CH.sub.3 (o.p.) "     284 " " " 2-NHCOCH.sub.3 5-OCH.sub.3 " " OC.sub.2 H.sub.4 OC.sub.6     H.sub.5 reddish orange 285 2-OC.sub.6 H.sub.5 H H 2-CH.sub.3 5-CH.sub.3     " " " golden yellow 286 " " " " " " " OC.sub.2 H.sub.4 C.sub.6 H.sub.5 "     287 " " " 2-OCH.sub.3 " " " " " 288 " " " " " " " OC.sub.2 H.sub. 4     OC.sub.6 H.sub.5 brownish yellow 289 " " " " 5-OCH.sub.3 " " " bright     red 290 " " " " " " " OC.sub.2 H.sub.4 C.sub.6 H.sub.5 " 291 " " " " "     2-CH.sub.3 " " bright red 292 " " " " " " " OC.sub.2 H.sub.4 OC.sub.6     H.sub.5 " 293 " " " " " H " OSO.sub.2 C.sub.6 H.sub.5CH.sub.3 (p) orange     294 " " " 2-OC.sub.2 H.sub.5 5-OC.sub.2 H.sub.5 " " " " 295 " " " " " "     " OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 bright red 296 " " " " " " "     OC.sub.2 H.sub.4 C.sub.6 H.sub.5 " 297 " " " "  2-CH.sub.3 " " " " 298 "     " " " " " " OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 " 299 " " 5-Cl " " " " " "     300 " " " 2-OCH.sub.3 5-OCH.sub.3 H H OC.sub.2 H.sub.4 OC.sub.6 H.sub.5     bright red 301 " " " " " " " OC.sub.2 H.sub.4 C.sub.6 H.sub.5 " 302 " "     " " " " " OSO.sub.2 H.sub.4 C.sub.6 H.sub.5 orange 303 " " " " "     2-CH.sub.3 " " " 304 " " " 2-OC.sub.2 H.sub.5 5-OC.sub.2 H.sub.5 H "     OSO.sub.2 C.sub.6 H.sub.4CH.sub.3 (p) " 305 H OCH.sub.3 H 2-OCH.sub.3     5-OCH.sub.3 2-C.sub.6 H.sub.5 " OC.sub.2 H.sub.4 C.sub.6 H.sub.5 " 306 "     " " " 5-NHCOCH.sub.3 H " " " 307 " " " " " " " OC.sub.2 H.sub.4 C.sub.6     H.sub.5 " 308 " OC.sub.2 H.sub.5 " " " " " OSO.sub.2 H.sub.4CH.sub.3 (p)     " 309 " OC.sub.2 H.sub.5 " " " " " OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 "     310 " " " " " " " OC.sub.2 H.sub.4 C.sub.6 H.sub.5 orange 311 " " " "     5-OCH.sub.3 " " " bright red 312 " " " 2-OC.sub.2 H.sub.5 5-OC.sub.2     H.sub.5 " " " " 313 " " " 2-OCH.sub.3 5-NHCOCH.sub.3 3-CH.sub.3 "     OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 orange 314 " OCH.sub.3 " 2-OC.sub.2     H.sub.5 5-OC.sub.2 H.sub.5 2-CH.sub.3 " " bright red 315 2-OCH.sub.3 H "     2-OCH.sub.3 5-NHCOCH.sub.3 H H OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 orange     316 H OCH.sub.3 " " 5-OCH.sub.3 " " OC.sub.2 H.sub.4 C.sub.6      H.sub.5CH.sub.3 (o,p) " 317 " N(CH.sub.3)COCH.sub.3 " " " " " OC.sub.2     H.sub.4 OC.sub.6 H.sub.5 bright red 318 " " " " " " " OC.sub.2 H.sub.4     C.sub.6 H.sub.5 " 319 " " " " " 2-CH.sub.3 " " " 320 " " " 2-OC.sub.2     H.sub.5 5-OC.sub.2 H.sub.5 H " OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 " 321 "     " " 2-OCH.sub.3 5-CH.sub.3 " " " reddish orange 322 " " " " " 2-CH.sub.3     " OC.sub.2 H.sub.4 C.sub.6 H.sub.5 " 323 " " " 2-CH.sub.3 " " " " orange     324 " " " " " " " OCH.sub.2 H.sub.4 C.sub.6 H.sub.5 " 325 " " " " " " "     OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 " 326 3-NO.sub.2 H " " " " " " golden     yellow 327 " " " " " " " OC.sub.2 H.sub.4 C.sub.6 H.sub.5 " 328 " " "     2-OCH.sub.3 " " " " orange 329 " " " 2-CH.sub.3 " " " OCH.sub.2 H.sub.4     C.sub.6 H.sub.5 golden yellow 330 3-NHCOCH.sub.3 " " " " " " " " 331 " "     " " " " " OC.sub.2 H.sub.4 O.sub.6      H.sub.5 " 332 H OCH.sub. 3 " 2-NHCOCH.sub.3 H 2-Cl 5-Cl OC.sub.2     H.sub.4 C.sub.6      H.sub.5 "

    __________________________________________________________________________    Example                                                                            Formula                       Hue                                        __________________________________________________________________________    333                                                                                 ##STR40##                    brownish orange                            334                                                                                 ##STR41##                    "                                          335                                                                                 ##STR42##                    yellowish brown                            336                                                                                 ##STR43##                    "                                          337                                                                                 ##STR44##                    "                                          338                                                                                 ##STR45##                    brownish orange                            339                                                                                 ##STR46##                    orange brown                               340                                                                                 ##STR47##                    "                                          341                                                                                 ##STR48##                    brownish orange                            342                                                                                 ##STR49##                    "                                          343                                                                                 ##STR50##                    "                                          344                                                                                 ##STR51##                    yellowish brown                            345                                                                                 ##STR52##                    orange                                     346                                                                                 ##STR53##                    "                                          347                                                                                 ##STR54##                    reddish orange                             348                                                                                 ##STR55##                    orange                                     349                                                                                 ##STR56##                    "                                          350                                                                                 ##STR57##                    "                                          351                                                                                 ##STR58##                    brownish orange                            352                                                                                 ##STR59##                    "                                          353                                                                                 ##STR60##                    orange                                     354                                                                                 ##STR61##                    "                                          355                                                                                 ##STR62##                    "                                          356                                                                                 ##STR63##                    "                                          357                                                                                 ##STR64##                    "                                          358                                                                                 ##STR65##                    yellowish brown                            359                                                                                 ##STR66##                    "                                          360                                                                                 ##STR67##                    "                                          __________________________________________________________________________

EXAMPLE 361

A fabric consisting of 65 parts of polyester fibers and 35 parts ofmercerized cotton is impregnated with a liquor which contains 70 g/l ofa 20% strength aqueous formulation of a water-insoluble dispersed dye ofthe formula ##STR68## and 80 g/l of a swelling agent and dye solventwhich comprises 80% of a polyethylene glycol of molecular weight 1,500and 20% of a reaction product of 1 mole of hexamethylenediamine and 15moles of ethylene oxide. The pH of the liquor is brought to 6 withcitric acid. The impregnated fabric is dried for 60 seconds at 120° C.and is then additionally heated for 60 seconds at 215° C. to fix thedye. It is then rinsed cold and warm and soaped for 20 minutes at 100°C. in the presence of a commercial detergent. A golden yellow dyeinghaving very good lightfastness, washfastness and rubfastness isobtained.

We claim:
 1. A process for dyeing cellulose-containing textile materialwhich comprises contacting a cellulose-containing textile material withwater and an oxyethylene or oxypropylene compound, thereby to swell thecellulose fibers of said textile material and dyeing said swollen fiberswith a dye of formula I ##STR69## where R is an aliphatic,cycloaliphatic, araliphatic or aromatic radical and n is 0 or 1, andwhere the rings A, B and C may be substituted and/or may carry a fusedring.
 2. A process as claimed in claim 1, wherein a dye of the formula Iwhere the radical ##STR70## is used.
 3. A process as claimed in claim 1,wherein a dye of the formula I is used, where the ring B isunsubstituted or is substituted by chlorine, methyl, acetylamino or C₁--C₄ -alkoxy or carries a fused benzo ring.
 4. A process as claimed inclaim 1, wherein a dye of the formula I is used, where the ring C isunsubstituted or is substituted by chlorine, methyl, methoxy, ethoxy orphenyl.
 5. A process as claimed in claim 1, wherein a dye of the formulaI is used, where the ring A is unsubstituted or is substituted bychlorine, bromine, methyl, ethyl, methoxy, ethoxy, phenoxy, nitro,cyano, unsubstituted or methyl-, O(SO₂)_(n) R-, chlorine-, bromine-,nitro- or cyano-substituted phenylazo, methylsulfonyl, ethylsulfonyl,phenylsulfonyl, SO₂ OR, COOR, ##STR71## R¹ being hydrogen, C₁ -C₄ -alkylor C₁ -C₄ -alkoxy-C₂ -C₃ -alkyl and n and R having the meanings given inclaim
 1. 6. A process as claimed in claim 1, wherein a dye of theformula I is used, where either n=0 and R is C₁ -C₁₂ -alkyl which isoptimally interrupted by oxygen and is unsubstituted or is substitutedby phenoxy, phenyl, tolyl or chlorophenyl, or n=1 and R has any of theabove meanings or is unsubstituted or chlorine- or methyl-substitutedphenyl.
 7. A process as claimed in claim 1, wherein a dye of the formula##STR72## is used, where R and n have the meanings given in claim 1 or 6and the rings C may be substituted.
 8. A process as claimed in claim 1,wherein a dye of the formula ##STR73## is used, where the rings A, B andC may be substituted and R is a radical containing a phenyl group. 9.Cellulosic textile material which has been dyed according to claim 1.